2,5-Hexanedione → HCID 53738518, compound

HRID 1740993Notes

Reaction equation

HRID 1740993 reaction equation
[CH3:1][C:2](=O)[CH2:3][CH2:4][C:5](=O)[CH3:6].[NH2:9][C@@H:10]([CH3:13])[CH2:11][OH:12].C(OCC)(=O)C.CCCCCC>CO>[OH:12][CH2:11][C@@H:10]([N:9]1[C:2]([CH3:1])=[CH:3][CH:4]=[C:5]1[CH3:6])[CH3:13]

Participants

5

Reactant 3

HCID 80352,5-HexanedioneHCID 80307L-AlaninolHCID 21226206Ethyl acetate hexane

Product 1

HCID 53738518HCID 53738518, compoundYield 96.3%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

2,5-Hexanedione (3.6 mL, 30.7 mmol) was added to a solution of (S)-2-amino-1-propanol (2.44 g, 32.5 mmol) in 15 mL of methanol. The mixture was stirred at reflux for 2 h. After concentrating in vacuo, the residue was dissolved in 100 mL of ethyl acetate and washed with 50 1 mL of saturated aqueous sodium bicarbonate and 50 mL of saturated aqueous sodium chloride. The organic layer was dried (sodium sulfate), decanted, and evaporated to give a yellow solid. Flash column chromatography on 150 g of silica gel using 2.5 L of 15% ethyl acetate/hexane to furnish 4.53 g (96% yield) of (S)-1-(2-hydroxy-1-methylethyl)-2,5-dimethylpyrrole as a white solid.

Workup

  1. temperatureat reflux for 2 h
  2. concentrationAfter concentrating in vacuo
  3. dissolutionthe residue was dissolved in 100 mL of ethyl acetate
  4. washwashed with 50 1 mL of saturated aqueous sodium bicarbonate and 50 mL of saturated aqueous sodium chloride
  5. dry with materialThe organic layer was dried (sodium sulfate)
  6. customdecanted
  7. customevaporated
  8. customto give a yellow solid

Sources & evidence

ORD record
ord-134437e9ddec454c8b578a39766f04e1
Source dataset
uspto-grants-1999_10
Patent number
US05972975

Reaction notes

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